Survival Guide for an Introverted CEO

Twenty years ago, I was unbelievably shy. I’d only meet new people because there was no way to avoid it. When you live in a campus dorm, it’s almost impossible to plunge into holy solitude. You’re pushed to talk to people. After a couple of years there, I was more adapted to life. I learned to drink beer and belt out Pink Floyd accompanied by moderate quality guitar playing. I must note that alcohol, guitar, and shouting Pink Floyd songs can transform any introvert into a decent person, interesting to talk to.

I kept my introversion through several jobs. It was with me when I was an HTML coder, a project manager, a programmer, a project manager again, a programmer again, and, finally, a CEO. So what is it like to be an introverted CEO of a product company? 👀

1. 😓 For a very long time, I was nervous about any direct conversation with a potential or actual client. As a result, I never initiated such talks. I would deal with this by emailing as much as possible. Anyway, when the company got more large clients, it was no longer possible to escape the talking—and so I had to learn how to handle actual real-time calls. I saw the first client IRL at a conference in Chicago. This was five years after we started product development. Actually, even now, I semi-consciously minimize the number of conversations with clients. Due to my personality type, it’s still much more convenient for me to read their texts and work with them asynchronously. Sure thing, after that many years in the company, I no longer worry before talking to someone, but I’m not proactive with it, either. For a CEO or a PO, it’s a vice because personal contact is essential. At the same time, nowadays, we get so much product feedback that personal conversations hardly add anything to the picture. So here we go with the first tip for introverted CEOs. At the product’s early stage, try to get over yourself and communicate in person a lot; at the later stage, you can be more selective with it.

2. 🤑 I hate selling. Too bad that sales are one of the main tasks of a CEO. Selling your product, selling your company to potential investors, and selling your company to reporters. Many CEOs seem to live in jets, visit dozens of conferences and key clients, and enjoy talking to the press, public speaking, and networking (an extrovert thing it is!). I don’t like any of this. My second tip is that it’s vitally important for a company to have someone who can and would enthusiastically do it. Good news: as a company founder, you can delegate this very well.

3. 👨‍💻 I felt extremely uneasy about one-on-one conversations with my employees (uneasy to the same extent as I am about the whole idea of management). I persistently tried to dodge this practice until I had no choice. Over time, I learned to “feel” people better, and now these conversations turn out insightful and helpful. But I still have to step out of my comfort zone to initiate one. This step is getting easier, too.

4. 💬 Long story short, everything related to relationships with other people is challenging to me. Just because I’m an introverted person. But for the sake of my leadership position, I do make efforts, and slowly, piece by piece, I adopt some elements of extraverted behavior.

5. ✍ I write a lot. Text is one of the best ways to communicate. Its excellent feature is storing information for a long time. Face-to-face talks fade from memory; we all forget discussions, however exciting they are; and it’s impossible to get back to them. You can always get back to a text, though, and check what we decided there, where we went and what happened in the end. Texts of all kinds help a lot to reflect on the entire evolution of your company. I also turn my every keynote speech into text. Luckily, introverts love writing. I wrote countless documents, posts, and articles to help myself and others (especially every other introverted engineer and/or entrepreneur) to analyze various situations. Besides, posts of all kinds are an excellent marketing tool. They helped our company a lot in the early stages of development.

6. 📊 I’ve always been product-focused. Working with information is my quiet strength, so to speak: I’m good at finding and analyzing trends, locating problems, and figuring out sound solutions. An extroverted CEO wouldn’t fancy this tiresome job, but I really like it. Somehow, it’s a lot like being a hardcore scientific researcher, and I think it’s beautiful.

7. 📚 I read a good many books—about 40 a year with no extra efforts invested. Extroverted leaders have their ways of getting information from sources like seminars, conferences, and talks. That’s cool, but I’m used to learning from books. Reading is a hell of meditative activity. When you read, a variety of concepts emerges and unfolds in your head. And so you can come up with some fresh ideas. So here’s my seventh piece of advice. Read a lot, and try to delve into multiple domains of knowledge. Because the most amazing insights spring up where different domains meet.

8. 🧩 I focus primarily on what happens inside the company. Hence my interest in the product, the culture, people, and the general working atmosphere. Consequently, I have less time and attention for sales and PR. I actually don’t believe that one person could have all the personality traits and qualities of an “ideal great CEO.”

Looking back, I realize how inexperienced and insecure I was when I started in the leadership role. Perhaps, it’s just now that I am self-confident and have some kind of personal balance. I smoothly go about things that I couldn’t have imagined twenty years ago. Apparently, though, I’ll never become fond of networking and will forever sincerely hate small talk.

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